| 100% | PETE | 4 | Officemate of Don and Peggy on "Mad Men" |
| 50% | PETE | 4 | Colleague of Don on "Mad Men" |
| 43% | DALE | 4 | Hank and Peggy's neighbor on "King of the Hill" |
| 41% | CARA | 4 | Buono of Mad Men and Stranger Things |
| 41% | DRAPER | 6 | Don or Betty on "Mad Men" |
| 41% | DRAPER | 6 | Don __ protagonist of Mad Men |
| 41% | ALAN | 4 | One of the men on "Two and a Half Men" |
| 40% | HENDRICKS | 9 | Christina __ of Mad Men and Good Girls |
| 39% | PEEL | 4 | Resort and fishing port on the west of the Isle of Man |
| 38% | SHIRT | 5 | Western ___, piece of men's clothing with a stylized yoke on the front and back |
| 37% | ABE | 3 | Peggy's boyfriend on "Mad Men" |
| 36% | FRIARTUCK | 9 | Member of Robin Hood's band of men portrayed on screen by Ronnie Barker and Tim Minchin |
| 36% | MCFEELY | 7 | Last name of the delivery man on 18-Across/40-Across and "Daniel Tiger's 40-Across" |
| 36% | FRIARTUCK | 9 | Member of Robin Hood's band of men portrayed on screen by comedians Ronnie Barker and Tim Minchin |
| 36% | PAULGIAMATTI | 12 | "Cinderella Man" and "Sideways" actor who turned down the role of Michael Scott on "The Office": 2 wds. |
| 36% | ANNE | 4 | Actress Dudek of "House" and "Mad Men" |
| 35% | OLD | 3 | ___ Fashioned, popular cocktail which is also the signature drink of Don Draper in "Mad Men" |
| 35% | MALE | 4 | Of boys and men |
| 34% | AGENCY | 6 | Mad Men is about this kind of advertising business |
| 34% | RAHM | 4 | Actor Kevin of "Desperate Housewives" and "Mad Men" |
| 34% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 34% | PLUR | 4 | Of mice and men?: Abbr. |
| 34% | STEINBECK | 9 | Of Mice and Men author |
| 34% | JONHAMM | 7 | Don Draper's portrayer on "Mad Men": 2 wds. |
| 34% | JONHAMM | 7 | He played the 60s Mad Man Don Draper |
| 33% | BLOKE | 5 | Man, on the Isle of Man |
| 33% | MANCHA | 6 | Man of La __, Don Quixote musical |
| 33% | LAMANCHA | 8 | Don Quixote-inspired musical: Man of __ |
| 33% | AMERICANSOUL | 12 | 2019 drama series on BET based on the creation of television host Don Cornelius's legendary dance and music program: 2 wds. |
| 33% | MADISON | 7 | Mad Men was named after ad men on this NY avenue |